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Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Waterfront cottage with kitchen and patio

Photo gallery for Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Deck with awning and a Harbor View
Fun for kids as the water is shallow.
Living room opens onto deck; sofa unfolds to full size bed.
Dining area, opens onto deck; table expands for seating for 10!
Well equipped kitchen

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 592.9 sq m

Popular amenities

  • Parking available
  • Barbecue grill
  • Kitchen
  • Outdoor space

Explore the area

View map
St Leonard, MD
  • Place, Matoaka Beach
    ‪1 min drive‬
  • Place, Calvert Cliffs State Park
    ‪19 min drive‬
  • Place, Cove Point Lighthouse
    ‪24 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Convertible bed(s)

1 Double Futon

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

About this property

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Harbor Cottage. Relax on the deck overlooking the fishing and sailboats of Flag Harbor opening onto the Chesapeake Bay. Only a three minute walk to the big sand beach famous for fossils from the Miocene period. Very quiet and not crowded. Great fishing from the beach or charter a boat. Shallow water makes for great swimming for kids. Bring your well behaved dog to enjoy the beach and swimming with you.
We keep a vacant day between renters as a courtesy to our cleaners and our arriving guests. These dates are blocked on our calendar.

Washington DC or Annapolis is only one hour away, and the entire Chesapeake Bay area is steeped in American history. Just 15 minutes from the shops and restaurants of Solomons Island, and the terrific Marine Museum there. Many state and county parks for hiking. fossil hunting, and birdwatching.
PLEASE CONTACT ME BEFORE CLICKING "BOOK IT NOW"
Keywords: Vacation Rental Cottage, Beach House, dog

Add dates for prices

Amenities

Kitchen
Pet-friendly
Air conditioning
Outdoor space
Parking available
Water view

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Parents are responsible for toddler-proofing
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Events

No events allowed
Seating for 10 at the dining table. Ask me.
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Pets

Pets allowed: dogs (limit 2 total)
Well behaved dogs are welcome. Add $35. per dog.
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Turn off the lights, lock the doors and return the keys
Please leave the cottage as tidy as you found it. Put trash in outside barrels, leave the beach pass in the kitchen, put the key back in the lock box - and thank you very, very much!
Failure to complete these may result in a negative review from the host.
Well behaved dogs only - please pad the floor under the crate to protect the hardwood floor. Contact me if your dog as ever bitten man or beast.
Our beach is unguarded - swim, fish, and boat at your own risk. Clean-up after yourself and your dog on the beach and neighborhood. No fireworks.
Stay off the cliffs - they are a landslide danger and private property. Fossil hunt at the water line or in the surf for better results and safety.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: Seating for 10 at the dining table. Ask me.
Long-term renters welcome
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

About the area

St. Leonard

Located in St. Leonard, this cottage is on the waterfront. Flag Harbor Marina and Perigeaux Vineyards and Winery are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Fox Run Center and First Colony Shopping Center. R&J's PlayPark and Annmarie Sculpture Garden and Arts Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
St Leonard, MD

What's nearby

  • Flag Harbor Marina - 3 min walk - 0.3 km
  • Matoaka Beach - 1 min drive - 0.7 km
  • Jefferson Patterson Park and Museum - 16 min drive - 15.4 km
  • Calvert Cliffs State Park - 19 min drive - 18.5 km
  • Cove Point Lighthouse - 24 min drive - 23.7 km

Getting around

  • Ronald Reagan National Airport (DCA) - 73 min drive

Restaurants

  • ‪Vera's White Sands Beach Club - ‬17 min drive
  • ‪Gateway Restaurant & Lounge - ‬12 min drive
  • ‪The Tavern - ‬5 min drive
  • ‪Frying Pan - ‬14 min drive
  • ‪Linda's Produce Stand - ‬9 min drive

Frequently asked questions

Is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach pet-friendly?

Yes, this property allows dogs (limit 2 total).

What time is check-in at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Check-in begins at 3:00 PM.

What time is check-out at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Checkout is at 11:00 AM.

Where is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach located?

Situated on the waterfront, this cottage is within a 5-minute walk of Chesapeake Bay and Long Beach. Flag Harbor Marina and Northern Chesapeake Bay are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 140 out of 162 reviews
Rating 8 - Good. 20 out of 162 reviews
Rating 6 - Okay. 1 out of 162 reviews
Rating 4 - Poor. 1 out of 162 reviews
Rating 2 - Terrible. 0 out of 162 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Coleby M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet Chesapeake Getaway

Cozy spot on bay. Great for beach hikes and birdwatching.
Stayed 4 nights in May 2025

10/10 Excellent

Judy O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location w easy access to beach for fishing and shelling ! Cottage very clean and comfortable w a new kitchen , large dining table and big deck ! Stores and restaurants not far but beware they are closed on Mondays except fast food ! Very welcoming community A-big thank you to the owner the O’s
Stayed 4 nights in Aug 2025

10/10 Excellent

Steve M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Calvert Cliff's Refuel

Stayed here for about 3 weeks for a short term work assignment, very clean and pretty well stocked. No issues, I'd stay again.
Stayed 20 nights in Feb 2025

10/10 Excellent

Ellen R., New Market, Maryland (USA)

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Get-Away

This was our 3rd summer visit to this home. We love it and will visit again!
Stayed 6 nights in Aug 2023

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house with a great location

It was perfect for my wife and I , two adult sons, and a dog. The house was very well equipped and the location was great. Beautiful view of the marina across the street and a sort walk to the beach on the Bay.
Stayed 3 nights in Dec 2022

10/10 Excellent

susan d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beach heaven

This was an amazing trip. The cottage is just perfect. The beach is wonderful. I wouldn’t change a thing. Thank you.
Stayed 21 nights in Jun 2024

10/10 Excellent

Daniel S., Philadelphia, PA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Flags Harbor Cottage

We had a lovely time fossil hunting on a private beach on Chesapeake Bay. The property is well equipped and spacious for a family of four, the location is great for Bay activities- steps from the Bay itself, convenient to activities in the area such as museums and nature preserves, but still very quiet tucked away from most commercial activity in the immediate area.
Stayed 4 nights in Aug 2023

10/10 Excellent

jason s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

perfect

been staying at this perfect setting for years. ownership always gracious hosts. couldn't find a rental with better neighbors and accessibility to beach. look forward to next year.
Stayed 14 nights in Sep 2024

10/10 Excellent

susan d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

moms funeral

the cottage was just perfect thanks for everything.
Stayed 4 nights in Oct 2023

10/10 Excellent

Cathy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Recharge and Tranquility

This is our third year staying at this serene and peaceful property. Although the weather was dismal it did not deter us from enjoying a recharging and tranquil week. We will definitely be back next year and many more years to follow. Thanks for the memories!
Stayed 4 nights in Sep 2024

10/10 Excellent

Siobhan F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Home away from home

A cozy and comfortable place that is secluded from traffic, but close to necessary stores. We had a lot of rain during our stay, so we couldn't use the front porch as often as we would have wished, but even the best hosts can't control the weather! :) The kitchen was set up very well, with the plates, pots and pans necessary if you cooked there, along with some basic spices. There's a tea kettle if you are a tea drinker (I am!) and a coffee pot too. Overall, I'd go back if I ever wanted to visit that part of Maryland again.
Stayed 7 nights in Jul 2022

10/10 Excellent

Thor S., Western Carolinas

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Gem and Already Booked Again!

Having lived in So. MD for over 50 years before moving away, sadly, we had to return for the funeral of a dear and immediate family member. However; our stay at “Harbor Cottage on the Chesapeake w Dog Friendly Beach” wound up transforming our stay from sorrowful to one filled with great memories walking our dog and grandchildren along the beach and then enjoying the idyllic marina views off the front deck of the house. The neighborhood is a QUIET and CLEAN one and EVERYONE is extremely friendly. Best of all, it was a huge stress reducer to checkin to a rental rated for cleanliness that was actually …. clean! Terrific communications by and from the owners, also. We so enjoyed our stay at “Harbor Cottage on the Chesapeake w Dog Friendly Beach” we have already booked a return visit!
Stayed 4 nights in Jan 2024

10/10 Excellent

jason s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
stay was excellent as always. great Neiborhood to enjoy beach with family and dogs. host was a pleasure to deal with. look forward to another season.
Stayed 15 nights in Sep 2025

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great stay at Harbor Cottage. We stay there at least once a year and look forward to it every time. Can't beat the location, neighborhood or convenience to the private beach. The cottage is charming with a great view of Flag Harbor right across the street.
Stayed 4 nights in Oct 2025

10/10 Excellent

Jeannine C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We Our stay was perfect. The cottage was spotless and had everything we needed.The beach was a minute away and the view off the porch was great. We like to birdwatch and it was fantastic in the marina. We will definitely return.
Stayed 7 nights in Sep 2025

10/10 Excellent

edith f.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was just as listed. Beautiful house and neighborhood.
Stayed 4 nights in Sep 2025

10/10 Excellent

Pamela B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was everything as advertised and more!! We loved it so much that we could live there forever!!Katherine was awesome!!!
Our pup Winnie exhausted from exploring all day in her bed for the night.
My husband Bob enjoying the bay with Winnie.
Stayed 4 nights in Aug 2025

10/10 Excellent

marie w.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location, location, location! A wonderful stay at the Harbor cottage. Beautiful view inside the home of the harbor and having a beach, almost to yourself, a mere block away was priceless. Peaceful. Restful. Very comfortable home with most needed provisions. One hour to Washington DC also so can enjoy the city as well. Enjoyed my stay with my husband and two small pups very much.
Stayed 7 nights in Aug 2025

10/10 Excellent

Jason H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great little cottage in a quiet neighborhood with a small marina across the road. Katherine was a great host and messaged us the day of our arrival to let us know of storms in the area and informed us where flashlights were in case of a power outage. Overall the cottage was very clean and homey, it reminded me of my grandmother's place in Baltimore. All basic amenities in the kitchen are provided, if you need a small store to grab a few things from, there is a Dollar General not too far from the cottage. Any larger shopping trips needing a larger grocery store, they are about a 20-30 minute drive. No washer and dryer on site, but the laundromats are about the same distance away. There are some great beaches nearby including the one right by the cottage. We liked the beach at Flag Ponds Nature Park over Calvert Cliffs. Flag Ponds has more traffic, but it is a long beach with plenty of room. Calvert Cliffs is also nice, but there is a long hike (almost 2 miles each way) to get there. The Calvert Marine Museum is also nearby and was a great way to learn some local and rich history. This is also close to the fishing pier that our son was very excited to go to. Washington D.C. is about an hour away, so a day trip is very easy to do. The Steven F. Udvar-Hazy center in VA is a must do.
Stayed 6 nights in Jul 2025

10/10 Excellent

Virginia M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Harbor Cottage is located in a quiet neighborhood within walking distance to a private beach on the Chesapeake Bay. Lovely views of the marina from the deck and inside house. If you like to cook it has a spacious kitchen. The owner was very responsive to questions. We will definitely rent this property again.
Stayed 5 nights in Jun 2025

8/10 Good

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Short but sweet trip.

Our annual trip with our grand kids (5 and 10) on their spring break. We always try to go some place new but within an hour or so from their home near Alexander. This place fit us wonderfully! Kids had a ball! Loved the beach- easy walk! Too cold to swim but they loved the sand. Lots of special yhings to do in the area with a short drive. Kitchen was awesome, well stocked and clean. Not much yard to play in but didn’t need it with beach.
Stayed 5 nights in Apr 2025

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Always a Delight

We've had the pleasure of staying at Harbor Cottage multiple times. It's charm and location can't be beat. It is always spotlessly clean and has a cozy beachy feel. In a quiet neighborhood, right across a private lane from picturesque Flag Harbor, it's peaceful and feels out of the way, but is only a few minutes drive to area attractions like Calvert Cliffs and Solomons. The dog friendly community beach is 1/2 block walk (or drive) down the lane. We have spent hours there searching for fossil shark teeth, or just watching the bald eagles and ospreys fly. If you are visiting the area do yourself a favor and stay at Harbor Cottage!
Stayed 4 nights in Dec 2024

10/10 Excellent

Gloria V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect beachside retreat

This house was the perfect fit for our stay in st Leonard. The kitchen was well appointed and the facility was very comfortable. We would definitely stay here again.
Stayed 4 nights in Nov 2024

10/10 Excellent

Steve D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property we loved it

I will be back next year this location was great.
Stayed 5 nights in Oct 2024

10/10 Excellent

JoAnne M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing stay

This is a lovely home that is well equipped for all your needs. The kitchen has everything and there are many beach chairs to use at the beach a short walk away. You will have a parking pass if you would rather not walk.wouldrathernot not walk.
Stayed 5 nights in Oct 2024

About the host

Hosted by Katherine Nelson

Host profile image
We love this area for a quick get-a-way: our neighbors are friendly and helpful, and the beach is peaceful and beautiful! We enjoy watching the eagles and ospreys fish, and the large schools of fish that can be seen in the (usually) clear water.

Why they chose this property

We found this peaceful and friendly spot by chance - it's so close to the Washington DC area. The community is very dog-friendly, and when we are alone on the beach, they can romp in the waves off the leash. There aren't dangerous tides, and seldom rough water.

What makes this property unique

We have discovered the fun of fossil hunting, or just sitting at the beach and reading and re-charging our energies. The light, wind, and water are constantly changing. You can walk the beach for hours.

Languages:

English

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